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Outlook Modern Authentication login prompt freezing RRS feed

  • Question

  • I'm not quite sure where this question belongs but I'm posting it here because Outlook is the only thing being affected by this.

    Basically I migrated from an on premises Exchange server to Exchange online with modern authentication enabled.

    What is happening is a few users, so far 3 out of 65 have reported this to me, are being prompted to login every morning to Office 365 when they open Outlook. The problem is the login window that comes up freezes or is blank.

    The workaround is to kill Outlook, open another office application, I chose Word in this situation, and click the file tab then click account. Sign out of the office account and sign back in. Then Outlook opens without prompting.

    The strange thing is we can log out of windows and back in and they are not prompted to login to Office 365 when opening Outlook. Only the next morning will it prompt again. I'm not aware of any routines that run at night that would trigger this.

    This is the MSI version of Office 2016 on a Server 2016 terminal server running Citrix XenApp 7.14. Windows and Office are both up to date with Windows Updates.

    Any thought?

    Thanks,
    John Long

    Edit: I just tried opening Outlook on the terminal server and it froze on me with a blank window. It hasn't done this before to me. Something else is I left it open while typing this and it eventually brought up the login prompt and let me login. So there was a delay of about 2 minutes. The question is why is this happening, and why is Outlook prompting for a login every morning.

    Edit 2: I'm able to replicate this and it takes about 2 minutes before the login prompt will start responding and take input.


    • Edited by jlongjr Wednesday, March 7, 2018 4:34 PM
    Wednesday, March 7, 2018 4:11 PM

Answers

  • Hi, Sorry for not following up sooner. I did eventually figure it out. As you know, I migrated my users to Exchange online. Exchange is configured to use modern auth to support multi factor authentication. Skype for business is not configured for modern authentication. My guess is because Skype starts up automatically it was sending a request to exchange because of the Outlook integration causing this modern auth prompt to come up. Then people were opening outlook before logging into this prompt causing it to freeze.

     

    To work around this I started roaming the \AppData\Local folder using Citrix WEM. That appears to have fixed it.

    Of course however, I'm going to have to narrow down which folders in \AppData\Local need to be roamed that effect this because that folder can get quite large.

    For me this was specific to our RDS servers, however if you have desktops that use roaming profiles this might be an issue too. Very specific configuration however. I think the ultimate fix will be to enable Modern Authentication in SfB.

    Thanks,

    John


    • Edited by jlongjr Monday, March 26, 2018 2:58 PM
    • Marked as answer by jlongjr Monday, March 26, 2018 3:01 PM
    Monday, March 26, 2018 2:58 PM

All replies

  • So waiting 2 minutes does not appear to be the solution every time this happens. This is just crazy. I killed it, opened Word, signed out of office, back into office and then Outlook opened without prompting for a login.

    Wednesday, March 7, 2018 7:49 PM
  • Hi,

    If they log their account on another client, will the same issue occur?

    Have they tried creating a new profile to check the result?

    The issue why Outlook asks for password could be caused by many reasons. You could follow the steps from this link to see if issue continues.

    Do you have backup PST files opened in Outlook? If yes, try removing and re-adding to Outlook.

    Besides, if issue continues, we could repair Office to check the result. To do this, please go to Control Pane > Programs and Features. Right click your Office suit. Click Change and then click Repair.

    What's more, we could check Event Viewer to find out more information about why logon window crashed. Please paste detailed information from Event logs so that we can do more research on this issue.

    Any updates, please feel free to tell me.

    Regards,

    Perry



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    • Edited by Perry-Pan Thursday, March 8, 2018 6:39 AM
    • Proposed as answer by Perry-Pan Monday, March 19, 2018 9:35 AM
    • Unproposed as answer by Perry-Pan Monday, March 19, 2018 9:35 AM
    Thursday, March 8, 2018 6:38 AM
  • Thanks for the information.

    I can replicate this issue with my account and can say I do not have this problem on my desktop. The users on the remote desktop servers are in caching mode and the OST is stored on a network share. I have tried creating a new mapi profile. I have not created a new user profile though. Do you think a new user profile may be necessary?

    I have not done an office repair but will try to do that this evening.

    Are there any particular event ID's I should look for? I haven't dug into the event viewer yet but will do so and post anything that is noteworthy.

    Thanks,

    John

    Thursday, March 8, 2018 2:57 PM
  • Hi,

    If you have question about how to check the Application Event Log for Errors, you could refer to this link.

    Any updates after you tried the suggestions, please feel free to tell me.

    Regards,

    Perry



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    Friday, March 9, 2018 12:58 AM
  • Hi,

    Just checking in to see if the information was helpful. Please let us know if you would like further assistance.

    Regards,

    Perry


    Please remember to mark the replies as answers if they helped. If you have feedback for TechNet Subscriber Support, contact tnsf@microsoft.com.


    Click here to learn more. Visit the dedicated forum to share, explore and talk to experts about Microsoft Teams.

    Monday, March 12, 2018 12:59 AM
  • Hi,

    If you have question about how to check the Application Event Log for Errors, you could refer to this link.

    Any updates after you tried the suggestions, please feel free to tell me.

    Regards,

    Perry

    Hi Perry,

    The link you posted loops me back to this discussion. I was wanting to know if there were specific event ID's that I could look for that deal with Office 365 modern authentication.

    I was able to do a repair of office along with reinstall all of the updates for office 2016 on the master image and update all of the remote desktop/Citrix servers over the weekend. Unfortunately the login prompt froze for one user and I suspect another user as well.

    Here is a strange observation. This morning the experience is different between one user and myself. Here is a little bit more info as to what is going on when we login and maybe where the problem is.

    When we login Skype for Business is set to start. When Skype started for me, a modern authentication prompt came up. I logged in and it went away. I then logged into Skype. Then I opened Outlook and received no further prompts and it was connected and updated my inbox.

    I'm wondering if when I opened SfB if the modern auth prompt was because Skype was connecting to Exchange. I don't believe Modern auth is enabled for SfB. Is it possible that this is causing problems?

    Thanks,

    John


    • Edited by jlongjr Monday, March 12, 2018 3:15 PM
    Monday, March 12, 2018 3:13 PM
  • Hi,

    >>I was wanting to know if there were specific event ID's that I could look for that deal with Office 365 modern authentication.

    Have you checked Event Viewer to see the detailed error log regarding Outlook freezing? You could find the Event ID in it.

    >>I'm wondering if when I opened SfB if the modern auth prompt was because Skype was connecting to Exchange. I don't believe Modern auth is enabled for SfB.

    Currently, I haven't found any official articles about this situation.

    In case there are corrupted system files, please try using the System File Checker tool to repair missing or corrupted system files.

    1. Open command prompt from Start. (If you are not the administrator, please right click it and then choose “Run as administrator”)

    2.Type sfc /scannow

    3. Do not close this Command Prompt window until the verification is 100% complete

    What’s more, we could also try starting Outlook in safe mode and see whether this issue continues. This helps eliminate if the problem is related to any third party add-ins. To do this, please exit Outlook, press Win key + R to open the Run command, type outlook.exe /safe, press Enter.

    Please update detailed error logs for further assistance.

    If there are any updates, please don't hesitate to tell me.

    Regards,

    Perry


    Please remember to mark the replies as answers if they helped. If you have feedback for TechNet Subscriber Support, contact tnsf@microsoft.com.


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    • Proposed as answer by Perry-Pan Thursday, March 15, 2018 9:12 AM
    • Unproposed as answer by jlongjr Monday, March 26, 2018 2:49 PM
    Tuesday, March 13, 2018 7:03 AM
  • Hi, Sorry for not following up sooner. I did eventually figure it out. As you know, I migrated my users to Exchange online. Exchange is configured to use modern auth to support multi factor authentication. Skype for business is not configured for modern authentication. My guess is because Skype starts up automatically it was sending a request to exchange because of the Outlook integration causing this modern auth prompt to come up. Then people were opening outlook before logging into this prompt causing it to freeze.

     

    To work around this I started roaming the \AppData\Local folder using Citrix WEM. That appears to have fixed it.

    Of course however, I'm going to have to narrow down which folders in \AppData\Local need to be roamed that effect this because that folder can get quite large.

    For me this was specific to our RDS servers, however if you have desktops that use roaming profiles this might be an issue too. Very specific configuration however. I think the ultimate fix will be to enable Modern Authentication in SfB.

    Thanks,

    John


    • Edited by jlongjr Monday, March 26, 2018 2:58 PM
    • Marked as answer by jlongjr Monday, March 26, 2018 3:01 PM
    Monday, March 26, 2018 2:58 PM
  • Hi,

    So glad to see what you have found the fix and thank you for sharing here.

    If you have other problems, please feel free to post here.

    Have a nice day.

    Regards,

    Perry


    Please remember to mark the replies as answers if they helped. If you have feedback for TechNet Subscriber Support, contact tnsf@microsoft.com.


    Click here to learn more. Visit the dedicated forum to share, explore and talk to experts about Microsoft Teams.

    Tuesday, March 27, 2018 12:44 AM
  • It still happens, it's still possible it's related to Skype. My profile didn't load on a new terminal server and when outlook opened for the first time the modern authentication prompt froze. The roaming profile fix is just temporary.
    • Edited by jlongjr Friday, April 20, 2018 2:28 PM
    Friday, April 20, 2018 2:26 PM